WO2014055578A2 - Compositions de revêtement et articles formés à partir de celles-ci - Google Patents

Compositions de revêtement et articles formés à partir de celles-ci Download PDF

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Publication number
WO2014055578A2
WO2014055578A2 PCT/US2013/062946 US2013062946W WO2014055578A2 WO 2014055578 A2 WO2014055578 A2 WO 2014055578A2 US 2013062946 W US2013062946 W US 2013062946W WO 2014055578 A2 WO2014055578 A2 WO 2014055578A2
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WIPO (PCT)
Prior art keywords
coating composition
diisocyanate
composition
total weight
coating
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Application number
PCT/US2013/062946
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English (en)
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WO2014055578A3 (fr
Inventor
Rajan B. BODKHE
Stuart E. Fores
Leon Levitt
Craig M. MOSS
Michael A. Johnson
Original Assignee
3M Innovative Properties Company
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Application filed by 3M Innovative Properties Company filed Critical 3M Innovative Properties Company
Priority to CN201380052171.2A priority Critical patent/CN104968715A/zh
Priority to AU2013327440A priority patent/AU2013327440A1/en
Priority to JP2015535747A priority patent/JP2015535880A/ja
Priority to EP13777403.0A priority patent/EP2904040A2/fr
Priority to CA2887088A priority patent/CA2887088A1/fr
Priority to US14/432,828 priority patent/US20150267076A1/en
Publication of WO2014055578A2 publication Critical patent/WO2014055578A2/fr
Publication of WO2014055578A3 publication Critical patent/WO2014055578A3/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/08—Polyurethanes from polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/302—Water
    • C08G18/307—Atmospheric humidity
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/36—Silica
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • C08J2375/08—Polyurethanes from polyethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2237—Oxides; Hydroxides of metals of titanium
    • C08K2003/2241—Titanium dioxide
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
    • C08K2003/3045—Sulfates

Definitions

  • the present disclosure relates to one part moisture cure polyurethane based coating composition useful for selectively allowing water vapor to pass at controlled rates but imparting air and water resistance.
  • the composition of the present disclosure is used particularly for air and water barrier system for buildings.
  • Air and water barrier systems control movement of air and water, and specifically water vapor, across a surface of a structure, such as a building enclosure. In exterior walls, uncontrolled air flow is the greatest source of moisture and condensation damage. Indoor comfort is affected by air temperature, relative humidity, direction of airflow and surrounding surface temperatures. Indoor air quality is enhanced by air and water barrier systems by keeping pollutants out of building interiors and is an efficient barrier systems in way of keeping pollutants out. Pollutants include water vapor, suspended particulates, dust, insects, smells, etc. Air and water barrier systems have significant impact on electricity consumption and gas bills.
  • Air nonresidential buildings are estimated to reduce air leakage by up to 83 percent, saving on gas bill more than 40 % and reducing electricity consumption more than 25% according to simulations by the National Institute of Standards and Technology (NIST) of typical buildings without air and water barriers.
  • Water vapor is a key ingredient in corrosion and mold growth. Air and water barrier systems help prevent water vapor from being transported by air movement between exteriors and interiors of structures, such as buildings.
  • the present disclosure provides a coating composition
  • a coating composition comprising: (a) a one part moisture cure polyurethane comprising: an aromatic polyurethane prepolymer having backbone derived from polyether and at least one aromatic end group, wherein the coating composition comprises about 8 wt% to 90 wt% polyurethane prepolymer based on the total weight of the coating composition; (b) 2 to 60 wt% of an inorganic filler based on the total weight of the coating composition; and (c) 2 to 60 wt% of a solvent based on the total weight of the coating composition, wherein the coating composition, when cured, is a water- vapor semi-permeable, air and water barrier film.
  • the water-vapor semi-permeable, air and water barrier film has a permeability of 1 perm to 10 perms according to ASTM E 96.
  • the water-vapor semi-permeable, air and water barrier film has a permeability of 3 perms to 8 perms according to ASTM E 96.
  • the coating composition further comprises 0.01 to 5 wt% of a catalyst based on the total weight of the coating composition.
  • the coating composition further comprises a moisture trigger additive.
  • the moisture trigger additive is a bis(oxazolidine)-based moisture-triggered isocyanate.
  • the coating composition further comprises 0.5 wt% to 1.5 wt% of a defoamer based on the total weight of the coating composition.
  • the coating composition further comprises at least one of the following: 0.50 wt% to 10 wt% of a rheology modifier based on the total weight of the coating composition, 1 wt% to 60 wt% titanium dioxide based on the total weight of the composition, and 0 wt% to 60 wt% of a color pigment based on the total weight of the composition, and combinations thereof.
  • the coating composition further comprises a plasticizer, wherein the plasticizer does not react with the aromatic polyurethane prepolymer.
  • the coating composition is a liquid at ambient conditions.
  • the coating composition further comprises fillers.
  • the one-part moisture-curable polyurethane further comprises an aliphatic isocyanate trimer. In some embodiments, the one-part moisture-curable polyurethane further comprises a second end group derived from an aromatic isocyanate.
  • the aromatic isocyanate is derived from; 1,3-phenylene diisocyanate (m-phenylene diisocyanate), 1 ,4-phenylene diisocyanate (p- phenylene diisocyanate), 2,6-toluene diisocyanate (2,6-TDI), 2,4-toluene diisocyanate (2,4-TDI), 1,5- naphthalene diisocyanate, diphenyl oxide 4,4'-diisocyanate, 4,4'-methylenediphenyl diisocyanate (4,4- MDI), 2,4'-methylenediphenyl diisocyanate (2,4-MDI), 2,2'-diisocyanatodiphenylmethane (2,2-MDI), diphenylmethanediisocyanate (MDI), 3,3'-dimethyl-4,4'-biphenylene isocyanate (tolidine diisocyanate), 3,3'-
  • the coating composition has different end groups.
  • the polyether back bone has a number average molecular weight of at least 200 g/mol.
  • the present disclosure provides a cured coating composition
  • a cured coating composition comprising a one- part moisture-curable polyurethane comprising a polyether backbone and at least one end group derived from an aromatic isocyanate, wherein the cured coating composition has a permeability of 1 perm to 10 perms according to ASTM E 96. In some embodiments, the cured coating composition has a permeability of 3 perms to 8 perms according to ASTM E 96.
  • the present invention provides an article comprising a substrate coated with any of the aforementioned coating compositions or any of the aforementioned cured coating compositions.
  • the coating is continuous.
  • the present disclosure provides a method of coating a substrate surface comprising applying any of the aforementioned coating compositions according to a substrate surface and allowing it to cure.
  • the coating composition is applied at an ambient temperature of -20°C or higher.
  • layer refers to any material or combination of materials on or overlaying a substrate.
  • the term "separated by” to describe the position of a layer with respect to another layer and the substrate, or two other layers, means that the described layer is between, but not necessarily contiguous with, the other layer(s) and/or substrate.
  • the term "(co)polymer” or “(co)polymeric” includes homopolymers and copolymers, as well as homopolymers or copolymers that may be formed in a miscible blend, e.g., by coextrusion or by reaction, including, e.g., transesterification.
  • copolymer includes random, block, graft, and star copolymers.
  • micro permeable as used herein means a film having a permeability of 1 to 10 perms according to ASTM E 96.
  • diisocyanate refers to a compound containing two isocyanate groups.
  • polyisocyanate refers to a compound containing two or more isocyanate groups. Hence, diisocyanates are a subset of polyisocyanates.
  • an article having a continuous coating over a surface of a substrate may be a building envelope where the coating covers the entire outer surface of the building with no interruptions.
  • liquid as used herein means substances that have a definite volume but no fixed shape at ambient conditions.
  • Exemplary liquids useful in the present disclosure include solutions, mixtures, emulsions and suspensions where the primary component in such solutions, mixtures, emulsions and/or suspensions have a definite volume but no fixed shape at ambient conditions.
  • substrate means construction materials including but not limited to exterior cladding materials and exterior sheathing materials.
  • the present disclosure provides one component, moisture cure polyurethane coating
  • compositions that are useful in air and water barrier systems are useful in air and water barrier systems.
  • compositions can be applied by spray, liquid, roller, trowel, as an article and/or a film and are semipermeable to water vapor and non permeable to air and water.
  • the presently disclosed coating composition is liquid at ambient conditions.
  • the presently disclosed coating compositions include a one -part moisture-curable polyurethane comprising a polyether back bone and at least one end group derived from an aromatic isocyanate.
  • the polyether back bone has a number average molecular weight of at least 200 g/mol, more preferably 500 g/mol, and most preferably 1000 g/mole.
  • the one-part moisture-curable polyurethane includes a polyisocyanate.
  • Polyisocyanate means any organic compound that has two or more reactive isocyanate (— NCO) groups in a single molecule such as diisocyanates, triisocyanates, tetraisocyanates, etc., and mixtures thereof. Polyisocyanate also includes oligomeric or polymeric isocyanates. Cyclic and/or linear polyisocyanate molecules may usefully be employed. For improved weathering and diminished yellowing, the polyisocyanate(s) of the isocyanate component is typically aliphatic. Useful aliphatic polyisocyanates include, for example, bis(4-isocyanatocyclohexyl) methane such as available from Bayer Corp.,
  • IPDI isophorone diisocyanate
  • HDI hexamethylene diisocyanate
  • VESTANATE TMDI trimethyl hexamethylene diisocyanate
  • TMXDI m-tetramethylxylene diisocyanate
  • the polyisocyanates include derivatives of the above-listed monomeric polyisocyanates. These derivatives include, but are not limited to, polyisocyanates containing biuret groups, such as the biuret adduct of hexamethylene diisocyanate (HDI) available from Bayer Corp. under the trade designation
  • HDI hexamethylene diisocyanate
  • DESMODUR N- 100 polyisocyanates containing isocyanurate groups, such as that available from Bayer Corp. under trade designation “DESMODUR N-3300” or “DESMODUR N-3900”, as well as polyisocyanates containing urethane groups, uretdione groups, carbodiimide groups, allophonate groups, and the like.
  • the one-part moisture-curable polyurethane includes a bis(oxazolidine)- based moisture-triggered isocyanate.
  • the one-part moisture-curable polyurethane includes a polyether back bone and at least one end groups derived from an aromatic isocyanate.
  • the polyisocyanate component may comprise polyisocyanates or polyisocyanate mixtures based on one or more aromatic diisocyanates, such as, for example benzene diisocyanate; toluene diisocyanate (TDI); diphenylm.eth.ane diisocyanate (MDI); isomers of any thereof; 1,3-phenylene diisocyanate (m-phenylene diisocyanate), 1 ,4-phenylene diisocyanate (p-phenylene diisocyanate), 2,6-toluene diisocyanate (2,6- TDI), 2,4-toluene diisocyanate (2,4-TDI), 1,5 -naphthalene diisocyanate, diphenyl oxide 4,4'-diisocyanate,
  • both end groups are derived from the same aromatic isocyanate. In some embodiments, the end groups are derived from different aromatic isocyanates.
  • the coating composition comprises urethane bisoxazolidine latent hardener, IPDI ((isophorone diisocyanate) trimer.
  • the presently disclosed coating composition comprises at least 10 wt% one-part moisture-curable polyurethane, more preferably 20wt% one-part moisture-curable polyurethane, and most preferably 40 wt% one-part moisture-curable polyurethane, based on the total weight of the coating composition.
  • the coating composition comprises plasticizers.
  • the coating composition can be produced with additional use of plasticizers in which case the plasticizers used do not contain any groups reactive toward isocyanates.
  • Plasticizers useful in the coating compositions of this disclosure include esters of organic carboxylic acids or anhydrides thereof, such as phthalates, for example dioctyl phthaiaie, diisononyl phthaiate or diisodecyl phthalate, adipates, for example dioctyl adipate, azelates and sebacates.
  • dialkyl phthalates such as dimethyl- hexyi)-pththa3ates, dibutyl phthalate, diethyl phthalate, dioctyl phthalate, butyl octyl phthalate; dicyclohexyl phthalate, butyl benzyl phthalate; triaryl phosphates such as tricresyl phosphate, triphenyl phosphate, cresyliliphenyl phosphate; trialkyi phosphates such as trioctyi phosphate and tributyl phosphate; alkoxyalkyl phosphates such as trisbutoxyethyl phosphate: alkyl aryl phosphates such as octyldiphenyl phosphate; alkyl adipates such as di-(2-ethyihexyl)adipate, diisooctyl adipate, octyl decy
  • ingredients useful in the presently disclosed coating compositions include antifoaming agents, wetting and dispersing agents, rheology modifiers, catalysts, pigments, extenders, solvents, fillers, light stabilizers and/or UV absorbers, dehydrators, and color additives.
  • the presently disclosed coating compositions may comprise one or more additives, such as, for example, "JONCRYL(R) 61 1" (BASF Corporation) and/or "NEOCRYL B734" (DSM N.V.).
  • JONCRYL(R) 611 is a styrene-acrylic acid copolymer.
  • JONCRYL(R) 61 1 may be used as a dispersing agent in a moisture-curable coating composition to affect pigment dispersion and film-forming properties, for example.
  • NEOCRYL B-734 is a methyl methacrylate, n-butyl methacrylate copolymer resin.
  • NEOCRYL B734 may be used as a dispersing agent to affect pigment dispersion and film-forming properties, for example.
  • the presently disclosed coating compositions may comprise one or more pigments or fillers.
  • Useful fillers are typically solids that are non-reactive with the other components of the compositions of the invention.
  • Useful fillers include, for example, clay, talc, dye particles, pigments and colorants (for example, T1O2 or carbon black), glass beads, metal oxide particles, silica particles, ceramic microspheres, hollow polymeric microspheres (such as those available under the trade designation EXPANCEL 551 DE from Akzo Nobel, Duluth, Ga.), hollow glass microspheres (such as those available under the trade designation K37 from Minnesota Mining and Manufacturing Co., St Paul, Minn.), carbonates, metal oxides, silicates (e.g. talc, asbestos, clays, mica), sulfates, silicon dioxide and aluminum trihydrate.
  • ground or light calcium carbonate (with or without a surface- treatment such as a fatty acid, resin acid, cationic surfactant, or anionic surfactant); magnesium carbonate; talc; sulfates such as barium sulfate; alumina; metals in powder form (e.g., aluminum, zinc and iron); bentonite; kaolin clay; quartz powder; and combinations of two or more.
  • useful organic pigments include halogenated copper phthalocyanines, aniline blacks, anthraquinone blacks, benzimidazolones, azo condensations, arylamides, diarylides, disazo
  • condensations isoindolinones, isoindolines, quinophthalones, anthrapyrimidines, flavanthrones, pyrazolone oranges, perinone oranges, beta-naphthols, BON arylamides, quinacridones, perylenes, anthraquinones, dibromanthrones, pyranthrones, diketopyrrolo-pyrrole pigments (DPP), dioxazine violets, copper and copper- free phthalocyanines, indanthrones, and the like.
  • DPP diketopyrrolo-pyrrole pigments
  • useful inorganic pigments include titanium dioxide, zinc oxide, zinc sulphide, lithopone, antimony oxide, barium sulfate, carbon black, graphite, black iron oxide, black micaceous iron oxide, brown iron oxides, metal complex browns, lead chromate, cadmium yellow, yellow oxides, bismuth vanadate, lead chromate, lead molybdate, cadmium red, red iron oxide, Prussian blue, ultramarine, cobalt blue, chrome green (Brunswick green), chromium oxide, hydrated chromium oxide, organic metal complexes, laked dye pigments and the like.
  • the filler can also comprise conductive particles (see, for example, U.S. Patent Application Pub. No. 2003/0051807) such as carbon particles or metal particles of silver, copper, nickel, gold, tin, zinc, platinum, palladium, iron, tungsten, molybdenum, solder or the like, or particles prepared by covering the surface of these particles with a conductive coating of a metal or the like. It is also possible to use non- conductive particles of a polymer such as polyethylene, polystyrene, phenol resin, epoxy resin, acryl resin or benzoguanamine resin, or glass beads, silica, graphite or a ceramic, whose surfaces have been covered with a conductive coating of a metal or the like.
  • conductive particles see, for example, U.S. Patent Application Pub. No. 2003/0051807
  • non- conductive particles of a polymer such as polyethylene, polystyrene, phenol resin, epoxy resin, acryl resin or benzoguanamine resin, or glass beads
  • Preferred fillers include inorganic solids such, for example, talc, titanium dioxide, silica, zirconia, calcium carbonate, calcium magnesium carbonate, glass or ceramic microspheres, and combinations thereof. In some embodiments, titanium dioxide and/or calcium carbonate are preferred.
  • the coating composition of the present disclosure may comprise one or more pigment wetting agents or dispersants.
  • Pigment wetting agents and dispersants that may be useful in the present disclosure may include, for example, DISPERBYK(R)- 1 10 (BYK-Chemie GmbH),
  • the coating composition may comprise one or more rheology modifiers.
  • Rheology modifiers useful in the present disclosure may include, for example, BYK(R) 430, BYK(R) 431 (BYK-Chemie GmbH), Bentonite clays, and/or castor oil derivatives.
  • the presently disclosed coating composition may comprise one or more antifoaming agents.
  • Antifoaming agents useful in the present disclosure may include, for example, BYK(R) 077 (BYK-Chemie GmbH).
  • the presently disclosed coating compositions may comprise one or more light stabilizers and/or UV-absorbers.
  • Light stabilizers useful in the present disclosure may include, for example, TINUVIN(R) 292 (Ciba/BASF).
  • UV-absorbers that may find utility in the presently disclosed coating composition may include, for example, TINUVTN(R) 1 130 (Ciba/BASF).
  • the coating composition may comprise one or more dehydrators.
  • Dehydrators useful in the presently disclosed coating composition may include, for example, p-toluenesulfonyl isocyanate, isophorone diisocyanate, and/or hexamethylene diisocyanate.
  • the presently disclosed coating composition may comprise one or more catalysts, such as, for example, dibutyltin dilaurate or a tertiary amine, to accelerate the curing reaction.
  • Catalysts that may find utility in the present disclosed coating composition may include, for example, DABCO(R) T-12 (Air Products and Chemicals, Inc.) and/or l,4-diazabicyclo[2.2.2]octane.
  • Other useful catalysts for the present disclosure include, but are not limited to, those catalysts that include both ether and morpholine functional groups, e.g., with 2,2-dimorpholinoethyl ether and di(2,6-dimethyl morpholinoethyl)ether.
  • a useful catalyst is 4,4'-(oxydi-2, 1 -ethanediyl) bis-morpholine, which known in the trade as DMDEE and is commercially available under the trade designation "JEFFCATE DMDEE” from Huntsman Corp. (Houston, Tex.).
  • catalysts include, e.g., organo tin catalysts, e.g., dibutyl tin dilaurate, and bismuth catalysts.
  • organo tin catalysts e.g., dibutyl tin dilaurate
  • bismuth catalysts bismuth octoate is a very good moisture cure catalyst, but is not as stable as some catalysts during shipping and storage where the temperatures may reach about 65 °C.
  • the catalyst is preferably present in the presently disclosed coating composition in an amount of from about 0.05% by weight about 5% by weight, more preferably from about 0.1% by weight to about 2% by weight, most preferably from about 0.1% by weight to about 1% by weight.
  • the coating composition may comprise one or more additional additives. Additional additives that may find utility in the presently disclosed coating composition may include, for example, those commercially available under the trade designations BYK(R) 358, and/or BYK(R) 306 (BYK-Chemie GmbH).
  • the coating composition may comprise one or more solvents.
  • Solvent should be non-reactive with isocyanate and examples of such includes aliphatic, aromatic or araliphatic solvent which do not contain any cerivitinov-active hydrogen atoms but do preferably contain ether groups and/or ester groups and/or halogen atoms and/or nitrile groups and/or amide groups.
  • Suitable solvent include methoxypropyl acetate, methoxyethyl acetate, ethylene glycol diacetate, propylene glycol diacetate, glyme, diglyme, dioxane, tetrahydrofuran, dioxolane, tert-butyl methyl ether, ethyl acetate, butyl acetate, chloroform, methylene chloride, chlorobenzene, o-dichlorobenzene, anisole, 1,2-dimethoxybenzene, phenyl acetate, N-methyl-2-pyrrolidone, dimethylformamide, N,N- dimethylacetamide, dimethyl sulphoxide, acetonitrile, phenoxyethyl acetate and/or mixtures thereof, preferably solvent containing ether and ester groups, such as methoxypropyl acetate, acetone, 2-butanone, xylene, toluene, cyclohe
  • the presently disclosed coating composition is used to make an article having a substrate coated with a coating comprising the presently disclosed coating composition.
  • the coating is continuous.
  • thickness of the coating is varied to achieve desired permeability of the article.
  • the amount of aromatic polyurethane and molecular weight of polyether backbone used in the coating composition is varied to achieve desired permeability of the article.
  • the aromatic polyurethane and molecular weight of polyether backbone used in the coating composition and the thickness of the coating are varied to achieve desired permeability of the article.
  • the present disclosure provides a film made using the presently disclosed coating composition.
  • the film has a permeability of 1 perm to 10 perms according to ASTM E 96.
  • the film has a permeability of 3 perms to 8 perms according to ASTM E 96.
  • the presently disclosed films have at least 100 % elongation and moisture vapor transmission rates of 1 perms to 10 perms according to ASTM E 96.
  • thickness of the coating is varied to achieve desired permeability of the film.
  • the amount of aromatic polyurethane with polyether backbone used in the coating composition, which is used in the film is varied to achieve desired permeability of the film.
  • the presently disclosed coating composition is useful in a method of coating a substrate surface including the steps of applying the presently disclosed coating composition to a substrate surface and allowing it to cure.
  • the coating composition is applied at an ambient temperature of -20°C or higher.
  • the present disclosure further provides a method for preventing air and water transport across a surface of a structure but allowing water vapor transport across the surface of the structure comprising (a) coating at least a portion of the surface of the structure with a coating composition comprising: a one -part moisture-curable polyurethane comprising a polyether back bone and at least one end group derived from an aromatic isocyanate.
  • a coating composition comprising: a one -part moisture-curable polyurethane comprising a polyether back bone and at least one end group derived from an aromatic isocyanate.
  • the structure is a building.
  • the coating composition, article and/or film is applied on construction materials including but not limited to exterior cladding materials and exterior sheathing materials.
  • Useful exterior sheathing materials include but are not limited to plywood, oriented strand board (OSB), foam insulation sheathing, nonwoven glass mat faced gypsum sheathing board, or other conventional sheathing materials commonly used in the construction industry.
  • Useful include but are not limited to exterior cladding layer brick, concrete blocks, reinforced concrete, stone, vinyl siding, fiber cement board, clapboard, or other known exterior siding materials.
  • a coating composition comprising:
  • a one part moisture cure polyurethane comprising: an aromatic polyurethane prepolymer having backbone derived from polyether and at least one aromatic end group, wherein the coating composition comprises about 8 wt% to 90 wt% polyurethane prepolymer based on the total weight of the coating composition;
  • the coating composition when cured, is a water- vapor semi-permeable, air and water barrier film.
  • any of the preceding embodiments further comprising at least one of the following: 0.50 wt% to 10 wt% of a rheology modifier based on the total weight of the coating composition, 1 wt% to 60 wt% titanium dioxide based on the total weight of the composition, and 0 wt% to 60 wt% of a color pigment based on the total weight of the composition, and combinations thereof.
  • composition of any of the preceding embodiments further comprising a plasticizer, wherein the plasticizer does not react with the aromatic polyurethane prepolymer.
  • composition of any of the preceding embodiments wherein the coating composition is a liquid at ambient conditions.
  • composition of any of the preceding embodiments further comprising fillers.
  • composition of embodiment 13 wherein the aromatic isocyanate is derived from; 1,3-phenylene diisocyanate (m-phenylene diisocyanate), 1 ,4-phenylene diisocyanate (p-phenylene diisocyanate), 2,6- toluene diisocyanate (2,6-TDI), 2,4-toluene diisocyanate (2,4-TDI), 1,5-naphthalene diisocyanate, diphenyl oxide 4,4'-diisocyanate, 4,4'-methylenediphenyl diisocyanate (4,4-MDI), 2,4'-methylenediphenyl diisocyanate (2,4-MDI), 2,2'-diisocyanatodiphenylmethane (2,2-MDI), diphenylmethanediisocyanate (MDI), 3,3'-dimethyl-4,4'-biphenylene isocyanate (tolidine diisocyanate), 3,3'
  • composition of embodiments 13 or 14 wherein the end groups are different.
  • composition of any of the preceding embodiments wherein the polyether back bone has a number average molecular weight of at least 200 g/mol.
  • a cured coating composition comprising a one-part moisture-curable polyurethane comprising a polyether backbone and at least one end group derived from an aromatic isocyanate, wherein the cured coating composition has a permeability of 1 perm to 10 perms according to ASTM E 96.
  • An article comprising a substrate coated with a coating comprising the coating composition of any of embodiments 1 to 16 or the cured coating composition of embodiments 17 or 18.
  • PTSI para-toluene suifonyl isocyanate obtained from Sigma- Aldrich Chemical Company, St. Louis, MO
  • CAB-O-SIL TS-720 Medium surface area fumed silica which has been surface modified with polydimethylsiloxane, obtained from Cabot Corp., Billerica, MA
  • Moisture vapor transmittance rate (MVTR) of the example samples described below were determined in accordance with the ASTM E96 (2010) “Standard test method for water vapor transmission of materials", obtained from IHS Inc., Englewood, CO
  • EX 1 -EX 10 samples were prepared from moisture cure polyurethane coating compositions made by mixing resins, pigments, specialty additives and solvents. Table 1, below summarizes the formulations for each of EX1-EX7 coating compositions. Table 2, below summarizes the formulations for each of EX8-EX10 coating compositions.
  • To prepare each coating composition the desired ingredients were charged into a mixing vessel. The vessel was placed in a mixer (dual asymmetric centrifuge mixer, obtained under the trade designation "150 DAC SpeedMixer” from Flacktek, Inc Landrum, SC) and the contents were mixed at 2500 rounds per minute (rpm) for 4 minutes.
  • the resulting slurries were then applied on a TEFLON sheet by using a drawdown coater (Multiple Clearance Applicator PA-5357 with a 40 mil (1.02 mm) clearance gap, obtained from BYK Gardner GmbH, Geretsried, MD) to form a coating with about a 40 mil (1.02 mm) wet thickness.
  • the coatings were allowed to cure at 20°C for 7 days. After curing the cured films were separated from the TEFLON sheet and the recovered cured film samples were tested.
  • MVTR of the cured EX 1 -EX 10 samples were determined and summarized in Table 3, below.
  • the tensile and elongation testing of the cured EX1- EX10 samples were determined and summarized in Table 4, below.

Abstract

L'invention porte sur une composition de revêtement comprenant : (a) un polyuréthane à un seul composant durcissant à l'humidité comprenant un prépolymère de polyuréthane aromatique ayant un squelette issu d'un polyéther et au moins un groupe terminal aromatique, la composition de revêtement comprenant environ 8 % en poids à 90 % en poids de prépolymère de polyuréthane par rapport au poids total de la composition de revêtement ; (b) 2 à 60 % en poids d'une charge inorganique par rapport au poids total de la composition de revêtement ; et (c) 2 à 60 % en poids d'un solvant par rapport au poids total de la composition de revêtement, la composition de revêtement, lorsqu'elle est durcie, étant un film barrière à l'air et à l'eau semi-perméable à la vapeur d'eau. L'invention porte également sur une composition de revêtement durcie et sur des articles formés à partir de celle-ci.
PCT/US2013/062946 2012-10-03 2013-10-02 Compositions de revêtement et articles formés à partir de celles-ci WO2014055578A2 (fr)

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CN201380052171.2A CN104968715A (zh) 2012-10-03 2013-10-02 涂料组合物及由其制得的制品
AU2013327440A AU2013327440A1 (en) 2012-10-03 2013-10-02 Coating compositions and articles made therefrom
JP2015535747A JP2015535880A (ja) 2012-10-03 2013-10-02 コーティング組成物及びそれらから製造される物品
EP13777403.0A EP2904040A2 (fr) 2012-10-03 2013-10-02 Compositions de revêtement et articles formés à partir de celles-ci
CA2887088A CA2887088A1 (fr) 2012-10-03 2013-10-02 Compositions de revetement et articles formes a partir de celles-ci
US14/432,828 US20150267076A1 (en) 2012-10-03 2013-10-02 Coating Compositions and Articles Made Therefrom

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US61/709,274 2012-10-03

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US9869098B2 (en) 2012-10-24 2018-01-16 Certainteed Corporation System, method and apparatus for manufactured building panel
USD809671S1 (en) 2013-10-22 2018-02-06 Certainteed Corporation Manufactured siding panel with frame
US10472293B2 (en) 2016-04-29 2019-11-12 Certainteed Gypsum, Inc. Building assembly containing a water barrier coating film and method of making the building assembly
WO2020000919A1 (fr) * 2018-06-26 2020-01-02 周连惠 Procédé pour la préparation d'un revêtement et d'un adhésif en polyuréthane ignifuges, antibactériens et à base aqueuse

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CN106030006B (zh) 2014-02-18 2020-06-05 3M创新有限公司 易于施用的空气和水阻挡制品
US11731394B2 (en) 2014-12-22 2023-08-22 3M Innovative Properties Company Air and water barrier articles
KR20180042298A (ko) 2015-08-18 2018-04-25 쓰리엠 이노베이티브 프로퍼티즈 컴파니 다공성 층 및 라이너를 갖는 공기 및 물 배리어 물품
CA3054558A1 (fr) 2017-02-23 2018-08-30 3M Innovative Properties Company Article pare-air et pare-eau comprenant une couche poreuse inelastique
CN108976379A (zh) * 2017-06-01 2018-12-11 天津市奇才防水材料工程有限公司 一种现浇防护片材及其制备方法
CN109321053B (zh) * 2018-09-14 2021-03-23 清远永昌涂料有限公司 一种基于热塑性丙烯酸树脂的刮涂型中涂汽车涂料及其制备方法
US11198790B2 (en) 2019-03-21 2021-12-14 Ddp Specialty Electronic Materials Us, Llc Water-resistive coating composition

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US9869098B2 (en) 2012-10-24 2018-01-16 Certainteed Corporation System, method and apparatus for manufactured building panel
US10682787B2 (en) 2012-10-24 2020-06-16 Certainteed Corporation Method and apparatus for fabricating a building panel
US11047134B2 (en) 2012-10-24 2021-06-29 Certainteed Llc Manufactured building panel
US11828071B2 (en) 2012-10-24 2023-11-28 Certainteed Llc Manufactured building panel assembly
USD809671S1 (en) 2013-10-22 2018-02-06 Certainteed Corporation Manufactured siding panel with frame
USD857922S1 (en) 2013-10-22 2019-08-27 Certainteed Corporation Manufactured siding panel with frame
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WO2020000919A1 (fr) * 2018-06-26 2020-01-02 周连惠 Procédé pour la préparation d'un revêtement et d'un adhésif en polyuréthane ignifuges, antibactériens et à base aqueuse

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WO2014055578A3 (fr) 2014-06-26
CA2887088A1 (fr) 2014-04-10
JP2015535880A (ja) 2015-12-17
AU2013327440A1 (en) 2015-04-30
EP2904040A2 (fr) 2015-08-12
US20150267076A1 (en) 2015-09-24

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